New PKS-NRPS tetramic acids and pyridinone from an Australian marine-derived fungus, Chaunopycnis sp.

2015 ◽  
Vol 13 (28) ◽  
pp. 7795-7802 ◽  
Author(s):  
Zhuo Shang ◽  
Li Li ◽  
Breno P. Espósito ◽  
Angela A. Salim ◽  
Zeinab G. Khalil ◽  
...  
Keyword(s):  
Tetramic Acid ◽  
Tetramic Acids

Marine-derived fungus Chaunopycnis sp. yielded the tetramic acid F-14329 (1) and new analogues, chaunolidines A–C (2–4), together with the new pyridinone chaunolidone A (5), and pyridoxatin (6).

Tetramic acid chemistry. Part 1. Reinvestigation of racemisation during the synthesis of tetramic acids via Dieckmann cyclisation

1990 ◽  
pp. 611 ◽  
Author(s):  
Jo�l Poncet ◽  
Patrick Jouin ◽  
Bertrand Castro ◽  
Louisette Nicolas ◽  
Mohamed Boutar ◽  
...  
Keyword(s):  
Tetramic Acid ◽  
Tetramic Acids

ChemInform Abstract: Tetramic Acid Chemistry. Part 1. Reinvestigation of Racemization During the Synthesis of Tetramic Acids via Dieckmann Cyclization.

ChemInform ◽  
1990 ◽  
Vol 21 (27) ◽  
Author(s):  
J. PONCET ◽  
P. JOUIN ◽  
B. CASTRO ◽  
L. NICOLAS ◽  
M. BOUTAR ◽  
...  
Keyword(s):  
Tetramic Acid ◽  
Tetramic Acids

scholarly journals Anti-Clostridium difficile Potential of Tetramic Acid Derivatives from Pseudomonas aeruginosa Quorum-Sensing Autoinducers

2009 ◽  
Vol 54 (2) ◽  
pp. 683-688 ◽  
Author(s):  
Chihiro Ueda ◽  
Kazuhiro Tateda ◽  
Manabu Horikawa ◽  
Soichiro Kimura ◽  
Yoshikazu Ishii ◽  
...  
Keyword(s):  
Clostridium Difficile ◽  
Pseudomembranous Colitis ◽  
Homoserine Lactone ◽  
Side Chain ◽  
Tetramic Acid ◽  
Gram Staining ◽  
Tetramic Acids ◽  
Bactericidal Activities ◽  
Staining Characteristic

ABSTRACT We have examined the potential bactericidal activities of several tetramic acids derived from Pseudomonas autoinducers against Clostridium difficile, a cause of antibiotic-associated pseudomembranous colitis. Clinical isolates of C. difficile (n = 4) were incubated in broth with a chemically synthesized Pseudomonas autoinducer and its tetramic acid derivatives. The structure-activity relationship and the mechanisms of action were examined by a time-killing assay and by determination of the morphological/staining characteristics. The use of some tetramic acids derived from N-3-oxododecanoyl l-homoserine lactone resulted in more than 3-log reductions in the viability of C. difficile within 30 min at 30 μM. The outer membrane was suggested to be one of the targets for the bactericidal activity of tetramic acid, because disturbance of the bacterial outer surface was demonstrated by alteration of the Gram-staining characteristic and electron microscopy. The data for the tetramic acid derivatives demonstrate that the keto-enol structure and the length of the acyl side chain of tetramic acid may be essential for the antibacterial activity of this molecule. These results suggest the potential for tetramic acid derivatives to be novel agents with activity against C. difficile.

Hybrubins: Bipyrrole Tetramic Acids Obtained by Crosstalk between a Truncated Undecylprodigiosin Pathway and Heterologous Tetramic Acid Biosynthetic Genes

2016 ◽  
Vol 18 (3) ◽  
pp. 572-575 ◽  
Author(s):  
Zhilong Zhao ◽  
Ting Shi ◽  
Min Xu ◽  
Nelson L. Brock ◽  
Yi-Lei Zhao ◽  
...  
Keyword(s):  
Tetramic Acid ◽  
Biosynthetic Genes ◽  
Tetramic Acids

scholarly journals The Biological and Chemical Diversity of Tetramic Acid Compounds from Marine-Derived Microorganisms

Marine Drugs ◽  
2020 ◽  
Vol 18 (2) ◽  
pp. 114
Author(s):  
Minghua Jiang ◽  
Senhua Chen ◽  
Jing Li ◽  
Lan Liu
Keyword(s):  
Biological Activities ◽  
Structural Complexity ◽  
Cyclopiazonic Acid ◽  
Chemical Diversity ◽  
Tetramic Acid ◽  
The Past ◽  
Acid Type ◽  
Tetramic Acids ◽  
Research Studies

Tetramic acid (pyrrolidine-2,4-dione) compounds, isolated from a variety of marine and terrestrial organisms, have attracted considerable attention for their diverse, challenging structural complexity and promising bioactivities. In the past decade, marine-derived microorganisms have become great repositories of novel tetramic acids. Here, we discuss the biological activities of 277 tetramic acids of eight classifications (simple 3-acyl tetramic acids, 3-oligoenoyltetramic acids, 3-decalinoyltetramic acid, 3-spirotetramic acids, macrocyclic tetramic acids, N-acylated tetramic acids, α-cyclopiazonic acid-type tetramic acids, and other tetramic acids) from marine-derived microbes, including fungi, actinobacteria, bacteria, and cyanobacteria, as reported in 195 research studies up to 2019.

scholarly journals Five Tetramic Acid Derivatives Isolated from the Iranian Fungus Colpoma quercinum CCTU A372

Biomolecules ◽  
2021 ◽  
Vol 11 (6) ◽  
pp. 783
Author(s):  
Gian Primahana ◽  
Abolfazl Narmani ◽  
Frank Surup ◽  
Rémy Bertrand Teponno ◽  
Mahdi Arzanlou ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Antimicrobial Activity ◽  
Ionization Mass ◽  
Rotating Frame ◽  
Tetramic Acid ◽  
Mucor Hiemalis ◽  
Configurational Analysis ◽  
Overhauser Effect ◽  
Planar Structures ◽  
Tetramic Acids

Submerged mycelial cultures of the ascomycete Colpoma quercinum CCTU A372 were found to produce five previously undescribed tetramic acids, for which we propose the trivial names colposetins A–C (1–3) and colpomenoic acids A and B (4 and 5), along with the known compounds penicillide (6) and monodictyphenone (7). The planar structures of 1–5 were determined by high-resolution electrospray ionization mass spectrometry (HR-ESIMS) and extensive 1D and 2D nuclear magnetic resonance (NMR) spectroscopy. Their absolute configurations were determined by the combination of electronic circular dischroism (ECD) analysis, J-based configurational analysis, and a rotating-frame Overhauser effect spectroscopy (ROESY) experiment. Colposetin B displayed weak antimicrobial activity against Bacillus subtilis and Mucor hiemalis (MIC 67 µg/mL).

Natural tetramic acids elicit multiple inhibitory actions against mitochondrial machineries presiding over oxidative phosphorylation

2021 ◽  
Author(s):  
Yufu Unten ◽  
Masatoshi Murai ◽  
Katsuyuki Sakai ◽  
Yukihiro Asami ◽  
Takenori Yamamoto ◽  
...  
Keyword(s):  
Oxidative Phosphorylation ◽  
Atp Synthase ◽  
Atp Synthesis ◽  
Anion Channel ◽  
Complex Iii ◽  
Tetramic Acid ◽  
Voltage Dependent Anion Channel ◽  
Saccharomyces Cerevisiae Mitochondria ◽  
Tetramic Acids ◽  
Fof1 Atp Synthase

Abstract The mitochondrial machineries presiding over ATP synthesis via oxidative phosphorylation are promising druggable targets. Fusaramin, a 3-acyl tetramic acid isolated from Fusarium concentricum FKI-7550, is an inhibitor of oxidative phosphorylation in Saccharomyces cerevisiae mitochondria, although its target has yet to be identified. Fusaramin significantly interfered with [3H]ADP uptake by yeast mitochondria at the concentration range inhibiting oxidative phosphorylation. A photoreactive fusaramin derivative (pFS-5) specifically labeled voltage-dependent anion channel 1 (VDAC1), which facilitates trafficking of ADP/ATP across the outer mitochondrial membrane. These results strongly suggest that the inhibition of oxidative phosphorylation by fusaramin is predominantly attributable to the impairment of VDAC1 functions. Fusaramin also inhibited FoF1-ATP synthase and ubiquinol-cytochrome c oxidoreductase (complex III) at concentrations higher than those required for the VDAC inhibition. Considering that other tetramic acid derivatives are reported to inhibit FoF1-ATP synthase and complex III, natural tetramic acids were found to elicit multiple inhibitory actions against mitochondrial machineries.

Biosynthetic strategies for tetramic acid formation

2021 ◽  
Author(s):  
Xuhua Mo ◽  
Tobias A. M. Gulder
Keyword(s):  
Molecular Mechanism ◽  
Gene Clusters ◽  
Acid Formation ◽  
Biosynthetic Gene ◽  
Tetramic Acid ◽  
Biosynthetic Gene Clusters ◽  
The Individual ◽  
First Time ◽  
Acid Unit

Over 30 biosynthetic gene clusters for natural tetramate have been identified. This highlight reviews the biosynthetic strategies for formation of tetramic acid unit for the first time, discussing the individual molecular mechanism in detail.

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